A Boss and his Car

I was on my day off midweek, and with the wife out to work, I thought I'd have a day lounging around the house doing as little as possible. When I'm lounging on my own, I like to sneak on a pair of my wife's pantyhose underneath my joggers as I love the feel of the nylon against my legs and the way my joggers glide over the nylon.

On this particular morning, as it was cold, I put on a pair of my wife's winter collection, a brown semi opaque pair - despite these are what she wore for work, there is a slight oily look when caught in the right light, and, in my opinion, look mighty fine on my legs!

After a quick breakfast and a brew, I lay on the bed, enjoying the naughtiness of my wife's nylon wear. My hand slid under the waistband of the joggers and I started playing slowly until soon my cock was rock hard. It was not long before I slid out my joggers and lay there solely in the tights, stroking myself through the 30D gusset.

The phone rang! I grabbed it quickly and saw it was my wife calling, luckily not on FaceTime!

"Hi hon," she said, "Are you busy today?"

"Er, no...not really." I replied.

"Good, fancy a quick earner? My boss needs a driver urgently and I told him you were off today. He's offered to pay you £70 to drive him to a business lunch and back again."

Not one to turn a quick buck down, I decided to take him up on the offer.

"Ok then, when?"

"Now," my wife said. "Be quick, and you'd better look smart - trousers, shirt and tie his usual driver wears."

"Ok, I'll be there in twenty mins" I said.

I quickly got off the bed and opened my wardrobe. I thought to hell with taking the tights off, no time for shorts or socks, I'll throw trousers over them quickly.

Fully dressed, I drove over to my wife's workplace and was met at the door by the boss. He was about twenty years older than me, but he was about my build and the ladies still loved him!

"Ah, good man, here's the keys!" and he pointed at a brand new Jaguar SUV.

I climbed into the driver's seat and he climbed in the back on the opposite side.

"Very kind of you to take up the job today, I'm having a working lunch, and I'm sure there'll be some drinks so I need a driver. My usual one phoned in sick today and left me short."

"Not a problem, sir", I responded - unsure as to why I said "Sir" but it seemed appropriate.

"Now you can take your time, I'm early as it is, get used to the car, the clutch can be kinda heavy."

With that I tried the clutch, and it was indeed heavy, compared to my car, and unusual in today's new cars. It was so heavy, the effort I needed to use lifted my trousers up somewhat.

As we were driving down the lanes to the restaurant, the road was getting windier and windier and I had to use the clutch more to change gear. Every time I did so, my trouser leg rode higher and higher.

"Good God man! Are those tights you are wearing? Well I never!"

"Er, sorry Sir, I thought if I was waiting for you to finish, it may be cold so I put a pair on to keep warm, save your fuel of course!" I said, thinking fast.

"Pull over at the next lay-by will you!" He ordered. He's going to kick me out because I'm wearing tights? Whatever next. How am I going to explain this to my wife? But pull up I did after five minutes. When I stopped, I looked in the rear view mirror at the boss, to see what he was going to do, but I felt, more than saw, a slap next to me, on the gear shift panel.

"There is the £70 I promised you for driving me." I looked and there indeed was cash where his hand had slapped down. "And there is another £30 if you drive the rest of the way without your trousers." He waved the money at me as I looked at him. A hundred pounds to drive a man whilst wearing tights. I could do that, I thought, and having murmured an agreement, I undid my belt, pulled my zip, unbuttoned the fly and then, having kicked my shoes off, I slid the trousers down my legs, revealing my wife's pantyhose. I folded the trousers and put them next to me then I lent forward to put my shoes back on so I could drive.

As I sat back up, the boss was climbing into the front next to me. Having closed the door I drove on. Neither of us saying a word, me concentrating on the road, thinking of the surrealness of the situation. After a couple of miles, the boss broke his silence.

"I do admire a man in tights, I really do. Do you mind?"

I looked at him, and thinking he meant did I mind him admiring my legs, I said no. I had misunderstood, obviously, because he then placed his large hand on my thigh. I was shocked that a man was actually touching me and there was not a lot I could do as I was driving. That said, despite it being a manly hand, the touch was soft, and alarmingly, heavenly against my nylon clad skin.

With his thumb and index finger, he created an arch and slowly dragged that from my knee to the top of my thigh, then he used the back of his fingers to glide back down to my knee. He continued this for another couple of miles, during which, I could feel a stirring between my legs. And I was not the only one that felt it.

"Ten miles to go, we'll be early, you can slow down!" he said, now moving his gentle fingers further up my thigh to brush against my cock, before moving back to my knee. He then reached across more to run his hand over my other leg, which so far had escaped any attention. His hand reached my thigh, then with the back of his hand, he transferred it back to my left leg by brushing against my balls and cock first.

"Yes I do admire men in tights," he said again, still stroking my thighs. "My wife is unaware of my interests in this area, and I would appreciate it that it stayed that way."

"Of course," I said, nervously.

"I'd also appreciate you not telling your wife either."

"Of course not." I exclaimed.

"Good, because if she does hear of this, then I will have to tell her that one of the men I've wanked was her husband!" And with that he gently, yet forcefully, pulled my dick clear of the tights and started wanking away.

I nearly crashed the car at that point and struggled to maintain a straight line on the road.

"Concentrate on not crashing, and I will concentrate on this," he said.

As I navigated the road, the boss was pulling down on my cock with a firm grip, then rolled my skin back over my head with gentle finesse. Occasionally he would massage the bulbous end of my now hard shaft, and then start stroking me again. He altered his rhythm on numerous occasions, presumably to see what I liked (or what nearly made me crash!).

After another couple of miles, his hand went exploring further down towards my balls. "Heavy," he said, "could do with lightening that load ''. He pinched my balls gently and then massaged them with his fingers as he used the base of his hand to rub my shaft.

I was unsure what I was letting myself in for. I was being touched up by my wife's boss, yet was it all my fault as I was wearing tights in the first place? He then paid me so he could admire my legs as I drove him. But fuck, what he was doing felt amazing. I looked back at him, and I saw he was taking a picture of his hand on my cock. "Insurance purposes son, just in case you tell my wife or yours."

"Don't think I'll be telling anyone soon," I said, as I settled back into driving and being wanked.

With two miles to go I had started getting used to driving while being wanked, though I was not sure I was comfortable with it being a man, yet it was expertly done, and dammit, it felt bloody good. We were nearing the restaurant and I was glad we were in an SUV because nobody walking or driving past could look in (thankfully there were no trucks on this road!). This was more so as we approached the last mile and boss man was building up the rhythm in his wrist to the point where I couldn't take anymore. Sensing my climax, he threw off his seatbelt, leant across and took me into his mouth as I exploded wave after wave of hot cum. He swallowed with mastery, pushing down on my knob then pulling up with his lips in time with my throbs. As the intensity died down, he still kept me in his mouth as he traced his tongue over my tip, between my bulbous head and the skin and right down my shaft, ensuring no cum remained. When he was sure he had it all he sat upright in his seat, got his bearings and simply said "We are here".

When I pulled into a parking space, he looked at me and told me to wait for him to get out then discreetly put my trousers back on."I'll be back in an hour and a half, there is a bistro round the side if you'd like a coffee. Put it on my tab. Now, I'm off to have a whisky before the others arrive so I can get rid of this taste. Tally ho!"

Having got my trousers back on, I went for a coffee in the Bistro that the boss had mentioned, and along with a nice cake, I put it on his tab. As I sat drinking, a text came through from an unknown number.

**I got your number from your wife**

Then

**Thought you may enjoy this as you wait**

Then a picture message. I was so shocked by the content I hid it quickly, making sure no one else saw it. When I looked around again, and saw no one would be able to see from where they were, I discreetly looked at it again. The picture was of mu knob. As well as the boss' hand. And my nyloned thighs. But fuck! Did my legs look good, my dick looked huge and the whole picture was hot to look at!

I felt myself getting hard again, thinking of what happened on the way here. Two hours ago, I wasn't even aware I'd be hired as a driver. And I got paid to be pleasured! OK, maybe that wasn't why I got paid, but still, money and wanked woohoo! Then I remembered I had just been masturbated by a man. Never ever expected that one. But it felt amazing, wrong, right, weird, hot and too far all at once. I had never expected to cheat on my wife (only with her tights). I felt guilty, but how did the boss feel? He obviously isn't new to this. Was there a secret society for things like this?

As I was draining the last of my coffee, another text arrived.

**Finishing early, meet you back at the car.**

I hurried back so I wouldn't keep the boss waiting and as I approached the car, the boss was with another man, similar age to him and just as lean.

"Here he is, good man! Thank you for cutting short your break. Not everyone were able to make it, so we had a quick lunch, a couple drinks and thought we'd head off home. Would you mind taking Barclay back? He lives on the way."

"Not at all sir," I replied.

"There we are Barclay, told you he was a sine chap!"

"Indeed he is." And with that, I got into the driver's seat and both gentlemen sat in the back. As we headed off, I felt relieved, yet secretly upset, that we now had company and that the morning's events may not be repeated. The picture of my cock being wanked was still in the forefront of my mind.

About seven miles down the road Barclay proclaimed "Next left good man, and that is my estate."

I turned left at the mentioned turning and drove steadily through a grand gate and up a long country drive. I could see a stately home far in the distance, amongst some trees and I started heading towards this, however Barclay advised me otherwise.

"Stop here in the cutting, behind the trees old boy! Something we'd like to see before we head back to the actual house."

"Yes sir." I replied and pulled into a clearing and into what looked like a lay-by hidden by trees.

"Excellent," the boss said, "I believe this is ideal Barclay, I really do! Now then, my fine man, and he slapped my shoulder cheerfully, "another £100 if you allow us to admire your legs!"

"I'm sorry sir?" I asked, knowing full well what he meant but unsure as to how this was going to go.

"Dammit man, get here in the back without your trousers! In fact, tell you what, get out of the car first so we can watch you step out of your trousers.!

I opened the door to get out and walked to the passenger side, away from the road. Both gents followed me round and stood against the car, ready for a strip tease. So tease them I would. A £100, easy money.

I started with my belt. I undid the clasp and slowly pulled it out of the trouser hoops until it was clear. Looking at both gents, I held my arm out to the side and dropped it. Then I slowly kicked my shoes off before unbuttoning my trouser button and slowly teasing the zip down. Once fully open, I lifted both my hands and the trousers slid slowly down my legs. I stepped out of the trousers then and stood there in just my shirt, tie and wife's pantyhose.

"Very nice," Barclay commented.

"Even better in full view," the boss said. "Now into the back so we can admire them up close."

Barclay jumped in first, then me and the boss followed, closing the door.

"Excellent" the boss said again, "I do admire men in tights Barclay, don't you?"

"Indeed I do. May I?" The latter question was undoubtedly to me, and though I knew what he meant following this morning's misunderstanding, I still said "Help yourself!"

Barclay placed his hand on my knee and moved it upwards towards my thigh. He was rougher than the boss, though the touch and the feel through the nylons was no less pleasant. The boss himself gently stroked my other leg. I put my head back onto the head rest and closed my eyes. If these two wanted to do this for £100, then I had no reason to deny them. In fact, I could feel my cock responding quicker this time than before, perhaps it was because of the attention of two this time?

I sat there content with the situation for easily five minutes and in that time, both gents had caressed my balls and cock, sometimes unintentionally, but mostly with purpose. Soon afterwards, I felt a little shift in Barclay. He had turned slightly as he was still stroking me, but his free hand had gone to his trousers to undo them. When opened, he stopped stroking me and used both hands to pull his trousers and underwear down. He then resumed stroking my leg but also that of his own cock with his other hand.

Now I felt nervous, this morning was my boss' hand and my cock - and only my cock. Now another one had emerged and I wasn't sure where this was going. As I was about to say something, the boss himself freed his manhood from his suit and pants and was masterly playing with himself and stroking the inside of my leg. I could see both gents were looking at my cock forcing a bulge in the pantyhose as they stoked their members. As there attention was on me, I looked at their cocks, now proud and free. I was still unsure about this and about to force my way out of the car when I suddenly realized that despite their age, the gents' manhoods were impressive. Despite being twenty years older than mine, they were large and looked formidable.

In that instance, my thoughts of escape disappeared and curiosity took over. What is it like to feel another man's cock. What is it like to wank another dick? How does it feel to pull the skin over another head? Well now I knew, because inadvertently, I discovered that my hands automatically reached out to take not just one cock, but both. As I sat there in the middle, I massaged their bulbous heads for what felt like minutes - I was obsessed. With my hands around their shafts, I was running my thumb over their heads and under the rims over and over. Barclay has started leaking some ooze, so I massaged this back into his head. During a rare moment where I was not watching either dick I looked at both men either side of me. They were sitting there, heads back, eyes closed. The only way I knew they were not dead was their constant murmurs of delight and their continual stroking of my legs, though this was now mainly focussed at the top of my legs, with my balls toyed by one and my cock the other - who had which I did not know; I was in my element, an element I never knew existed.

Now I knew how it felt to wank another cock, and the experience was different to when I play with myself. Though I myself considered my size a little larger than average, these gents were bigger than me. I had to find out how long they were, so after massaging their heads for quite a while, I took the plunge and pulled my hands down both their shafts. The boss appeared longer, but Barclay was definitely girthier and his balls solid. I continued this for a while, Barclay easier to wank because of my right hand tendency and also he was self lubricating with pre-cum. That said, I don't think the boss was complaining, despite my left hand action, though I did mention that he could do with lubing up.

"Fair enough," he replied cheerfully. "Barclay?"

"Yes old boy"

And with that they both shuffled round on the back seats to face each other. Luckily we were in the SUV so it wasn't too awkward for them, but still, they both had to stoop so they could be upright in the back. As a result, their cocks were hanging in front of my face facing each other. I took them both again in my hands, and realizing what they wanted me to do, I rubbed Barclay's tip onto the Boss's length so he could be lubed up, but I didn't stop there. I carried on wanking them both and then pulled them closer together so I could wank them together with one hand. As one cock had its skin pulled down, the other cock had its skin pulled up, and then vice versa each time I shifted direction. With my other hand I alternately played with their balls. Barclays was definitely more solid, but the boss looked as if his had been emptied fairly recently.

Naturally, their hands were not on my legs any longer, and they felt fairly lonely, however their hands were still busy. The boss had his hand on my shoulder for support while Barclay rested his on the back of my head. I had not really realized this until Barclay pushed my head towards his cock. As it got nearer, he turned slightly to push his bulging member into my mouth. He really did have to push because I was not willing to take him in my mouth, but as soon as he penetrated my sealed lips, I could taste him and for some reason that I still cannot fathom, this prompted me to allow his full length, despite at first, while slowly pushing himself into me, I could feel myself gag. When he felt this, he eased up, but then came back for more. I soon learnt how to tolerate his length and he pushed himself deeper every time. It is fair to say I did not suck Barclay, as he was most definitely fucking my face. He thrust and he thrust, sometimes deep, sometimes just the tip, sometimes very deep.

While my face was being fucked, my hand was still wanking away the boss, and here I felt some loyalty towards him. He swallowed my load this morning, it is only fair he was in my mouth and not Barclay, so I maneuvered his manhood in front of my face and at an opportune moment, I pulled off Barclay and took the boss into my mouth. Barclay still thrusting punched his cock against my mouth and the boss' cock, but my suction had held onto the boss and he remained engulfed in my mouth. Now I was sucking, and I was sucking fast. From the satisfied and approving noises he made, I guessed this is how the boss liked it, and soon I could feel his cock making those pre-climax spasms.

I pulled off him, wanting this moment to go on longer. I grabbed the base of his shaft to stop him ejaculating there and then. I did the same to Barclay to stop him thrusting into my mouth again. Now I had two large, bulging cocks, held tight at their shafts, in front of me. I took the boss back into my mouth - just his tip this time. Then I pulled him out and put Barclay's tip into my mouth. I traced my tongue over and under his rim. Then, daringly, I placed both tips together and wrapped my lips around them, flicking my tongue from one rim to another, sucking with my lips, and sometimes flicking my tongue between both their cum holes.

Now I wanted to see what other cum taste like. The thought hit me from nowhere, but tasting other men's cum was what I was going to do. I started with the boss as I knew he was near and so started bobbing up and down on his dick with vigour. I was right, and within several thrusts he exploded into my mouth. He was salty and tangy, not too unpleasant. Though I must have been correct about him emptying his balls recently as two throbs of stringy cum and then he slowed down. Though I hadn't swallowed each throb like he had this morning, I was pleased I didn't spill a drop and was able to swallow it all.